BR112016009977B1 - aqueous composition, methods to control phytopathogenic fungi and / or growth of undesirable plants and / or infestation of undesirable insects or mites and / or to regulate plant growth, to treat plants and to produce a composition, and, use of a carboxylic acid amide - Google Patents

Abstract

the present invention relates to an aqueous composition comprising a pesticide and a certain carboxylic acid amide. the invention also relates to a method for the control of phytopathogenic fungi and / or the growth of undesirable plants and / or infestation of undesirable insects or mites and / or to regulate the growth of plants, in which the composition is left to act on the respective pests, their habitat or the plants to be protected from the respective pest, on the soil and / or on undesirable plants and / or crop plants and / or their habitat. moreover, the invention relates to the use of carboxylic acid amide as a solvent for pesticides with low or no phytotoxicity. the present invention comprises combinations of preferred characteristics with other preferred characteristics.

Description

“WATER COMPOSITION, METHODS TO CONTROL PHYTOPATHOGENIC FUNGI AND / OR GROWTH OF UNDESIRABLE PLANTS AND / OR INFESTATION OF UNDESIRABLE INSECTS OR MITES AND / OR TO REGULATE PLANT GROWTH, FOR PLANT TREATMENT AND FOR PRODUCTION OF A COMPOSITION, AND A CARBOXYLIC ACID AMIDE ”[001] The present invention relates to an aqueous composition comprising a pesticide and a certain carboxylic acid amide. The invention also relates to a method for the control of phytopathogenic fungi and / or the growth of undesirable plants and / or infestation of undesirable insects or mites and / or to regulate the growth of plants, in which the composition is left to act on the respective pests, their habitat or the plants to be protected from the respective pest, on the soil and / or on undesirable plants and / or the crop plants and / or their habitat. In addition, the invention relates to the use of carboxylic acid amide as a solvent for pesticides with little or no phytotoxicity. The present invention comprises combinations of preferred characteristics with other preferred characteristics.

[002] A large number of liquid concentrates are available for agricultural markets, and each type of product has its advantages and disadvantages. For example, agrochemical pesticides have the advantages that they contain a high concentration of active ingredients, and the ability to incorporate various ingredients into the composition to increase the effectiveness of the composition. However, many agrochemicals, in particular technical grade pesticides, have a disadvantage in that they have to be dissolved before use, which can be dangerous because of low flash points, environmental toxicity of solvents and require substantial mixing and long dissolution times.

Petition 870160017377, of 05/03/2016, p. 12/57 / 34 [003] There is a great desire in the pesticide industry to find alternatives to commonly used solvents such as isophorone, MBK, NMP, etc., which can be expensive, difficult to source and / or are unattractive environmentally due to its inherent phytotoxicity, toxicity, for example, teratogenicity or regulatory status.

[004] Field tests have shown that certain environmentally friendly solvents may show a negative crop response with excess phytotoxicity.

[005] Thus, there is a need in the agricultural industry for solvents that are capable of keeping a wide variety of pesticides in solution and that have a reduced toxic response both to the environment and to the crop that is sprayed.

[006] Amides and their use in agrochemical formulations as solvents for inhibiting crystal formation are generally known: [007] EP 0 044 955 described the use of amides as a solvent for liquid herbicidal compositions comprising a pyridazone derivative and a biscarbamate .

[008] DE 43 41 986 describes the use of amides for inhibiting the formation of crystals in agricultural compositions, which comprise azole derivatives.

[009] WO 2008/101629 describes biocidal compositions comprising at least one dialkylamide based on oleic or linoleic acid, and at least one biocide in which said dialkylamides reduce the tendency to form crystals.

[0010] WO 2010/009829 describes that agricultural compositions comprising C8-C12 fatty acid biocides and dialkylamides in which said C8-C12 fatty acid dialkyl amides are considered excellent solvents for a wide variety of different herbicides, insecticides and fungicides.

Petition 870160017377, of 05/03/2016, p. 13/57

3/34 [0011] The amides described in the prior art are said to have good solvent properties and that they are capable of inhibiting the formation of crystals. However, the present inventors have found that certain carboxylic acid amides known in the art have a phytotoxic effect on plants.

[0012] It was, therefore, an object of the present invention to identify a carboxylic acid amide, which is well suited to solves pesticides and is less phytotoxic to plants. On the other hand, the carboxylic acid amide must make possible a formulation that is stable to the storage of pesticides.

[0013] The object was resolved by an aqueous composition comprising a pesticide and a carboxylic acid amide according to formula (A)

R2 where

RI is C2-C8 alkyl, and

R2 and R3, independently of each other, are C1 -C6 alkyl, with the proviso that R2 is not C1 alkyl when R3 is C1 alkyl, on the condition that if R2 and R3 are C4 alkyl and RI is C2 alkyl or , if R2 and R3 are C4 alkyl and RI is C3 alkyl or, if R2 and R3 are C3 alkyl and RI is C3 alkyl, the pesticide is not chloridazon, bromopyrazone or carbamate, and on the condition that if R2 and R3 are alkyl C2 and RI is C7-C8 alkyl or, if R2 and R3 are C3 alkyl and RI is C3-C5 alkyl or C7-C8 alkyl or, if R2 and R3 are C4 alkyl and RI is C2-C5 alkyl or C7- alkyl C8, the pesticide is not an azole derivative according to formula (B)

Petition 870160017377, of 05/03/2016, p. 14/57

4/34

(B)

Cl where

R ⁶ is

R ⁷ is tert-butyl and R ⁸ is hydroxyl, or

R ⁶ is 4-fluorophenyl, R ⁷ is 2-fluorophenyl and R ⁸ is hydroxyl, or

R ⁶ is 2,4-dichlorophenyl, R ⁷ is n-butyl and R ⁸ is hydroxyl, or

R6é

-CH — CH—

R ⁷ is phenyl and R ⁸ is cyan, or

R ⁶ is 2-chloro-benzyl, R ⁷ is 1-chloro-cycloprop-1-yl and R ⁸ is hydroxyl, or

R ⁶ is 4-chlorophenyl

R ⁷ is

and R ⁸ is hydroxyl;

and / or an azole derivative according to formula (C)

(C) where

Y is CH (OH) and R ⁹ is chlorine or phenyl, or

Petition 870160017377, of 05/03/2016, p. 15/57

5/34

Y is CO and R ⁹ is chlorine and / or an azole derivative according to formula (D) „10

R OH

Cl — çVcH = C-CH “C (CH ₃ ) ₃

where R ¹⁰ is hydrogen or chlorine, and / or 1 - ([bis- (4-fluorophenyl) -methyl-silyl] -methyl) -1 H- (1,2,4triazole) according to formula (E)

and / or 1- [3- (2-chlorophenyl) -2- (4-fluorophenyl) -oxyran-2-yl-methyl] 1H- (1,2,4-triazole according to formula (F).

[0014] The present inventors have surprisingly found that certain amides do not have or have only a minimal phytotoxic effect on plants, maintaining their property of resolving a wide range of pesticides.

[0015] In a preferred embodiment, R2 and R3 are C2C4 alkyl and RI is C2-C8 alkyl. More preferably, R2 and R3 are C2-C4 alkyl and

RI is C2-C7 alkyl. In an even more preferred embodiment, R2 and

R3 are C2-C4 alkyl and RI is C2 alkyl, in particular R2 and R3 are C4 alkyl and

RI is C2 alkyl. In another preferred embodiment, R2 and R3 are C4 alkyl and RI is C7 alkyl.

[0016] The term alkyl as used herein indicates, in each case, a straight or branched chain alkyl group. In the context of the present invention, straight chain alkyl also means medium linear alkyl.

Petition 870160017377, of 05/03/2016, p. 16/57

6/34

Examples of an alkyl group are methyl, ethyl, n-propyl, isopropyl, n-butyl,

2-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-di-methylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,

1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl, etc.

[0017] In another preferred embodiment, the present invention relates to an aqueous composition comprising a pesticide and a carboxylic acid amide according to formula (A)

I

R2 wherein R2 and R3 are alkyl C ₄ straight chain alkyl and RI is straight chain C7. Such carboxylic acid amides are also known as N, N-di-n-butyl-N-octanamide or N, N-di-n-butyl-caprylamide.

[0018] The term pesticide refers to at least one active substance selected from the group of fungicides, insecticides, nematicides, herbicides, phytotoxicity protectors, molluscicides, rodenticides and / or growth regulators. Preferred pesticides are fungicides, insecticides, herbicides and growth regulators. Especially preferred are pesticides, herbicides, fungicides and insecticides. Mixtures of pesticides from two or more of the above classes can also be used. The skilled artisan is familiar with such pesticides, which can be found, for example, in the Pesticide Manual, 14th Ed. (2006), The British Crop Protection Council, London. The pesticides described above can be combined with any carboxylic acid amide of the present invention. Suitable pesticides that can be combined with amides from

Petition 870160017377, of 05/03/2016, p. 17/57 / 34 carboxylic acid of the present invention are as follows:

A) strobilurins:

- azoxystrobin, dimoxystrobin, coumoxystrobin, coumetoxystrobin, enestroburin, fluoxastrobin, cresoximemethyl, metominostrobin, orisastrobin, picoxystrobin, pyraclostrobin, pyramethostrobin, piraoxystrophine, 2-pyloxymethyl-2-phenylphenyl-triloxymethyl-2-phenylphenyl - (2- (3- (2,6-di-chlorophenyl) -1methylalylidenoaminooxymethyl) phenyl) -2-methoxyimino-Nmethylacetamide;

B) carboxamides:

- carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boscalide, carboxin, fenfuram, fenhexamide, flutolanil, furametpir, isopirasama, isothianyl, quiralaxyl, mepronil, metalaxyl, metalaxyl-oxen, oxenoxamine, oxenoxamine, N- (2 (1,3-dimethylbutyl) phenyl) -1,3-dimethyl-5-fluoro-1H-pyrazol-4carboxamide), pentiopirad, silkxane, keyboardoftalam, tifluzamide, thiadinyl, 2-amino-4methyltiazole-5-carboxanilide , N- (3 ', 4', 5'trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methyl-1H-pyrazol-4carboxamide, N- (4'-trifluoromethylthiobiphenyl-2-yl) -3-difluoromethyl- 1methyl-1H-pyrazol-4-carboxamide, N- (2- (1,3,3-trimethylbutyl) -phenyl) -

1,3-dimethyl-5-fluoro-1H-pyrazol-4-carboxamide;

- Carboxylic acid morpholides: dimetomorf, flumorf, pirimorf;

- benzamides: flumetover, fluopicolide, fluopyrama, zoxamid;

- other carboxamides: carpropamide, diclocimet, mandipropamide, oxytetracycline, siltiofam, N- (6-methoxypyridin-3yl) cyclopropanecarboxamide;

C) azoles:

- triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole,

Petition 870160017377, of 05/03/2016, p. 18/57 / 34 diphenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, miclobutanil, oxpoconazole, tacobonazole, proponolazole, paclobazolazole, propylazol, , triadimenol, triticonazole, uniconazole;

- imidazoles: cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole;

- Benzimidazoles: benomyl, carbendazim, fuberidazole, thiabendazole;

- others: etaboxam, etridiazole, himexazole, 2- (4-chlorophenyl) -N- [4- (3,4dimethoxy-phenyl) isoxazol-5-yl] -2-prop-2-inyloxyacetamide;

D) heterocyclic nitrogen compounds

- pyridines: fluazinam, pyrifenox, 3- [5- (4-chlorophenyl) -2,3-di-dimethylisoxazolidin-3-yl] -pyridine, 3- [5- (4-methylphenyl) -2,3dimethylisoxazolidin3-yl] pyridine;

- pyrimidines: bupirimate, cyprodinil, diflumetorim, fenarimol, ferimzone, mepanipyrim, nitrapirin, nuarimol, pyrimethanil;

- piperazines: triforin;

- pyrroles: fludioxonil, fenpiclonil;

- morpholines: aldimorf, dodemorf, dodemorf acetate, fenpropimorf, tridemorf;

- piperidines: phenpropidine;

- dicarboximides: fluorimid, iprodione, procymidone, vinclozoline;

- 5-membered non-aromatic heterocyclic rings: famoxadon, phenamidone, flutianyl, octylinone, probenazole, S-allyl-5-amino-2isopropyl-3-oxo-4-orthotolyl-2,3-dihydro-pyrazol-1-thiocarboxylate ;

- others: acibenzolar-S-methyl, amisulbromo, anilazin, blasticidinaS, captafol, captan, quinomethionate, dazomet, debacarb, diclomezine, difenzoquat, difenzoquat methylsulfate, phenoxanil,

Petition 870160017377, of 05/03/2016, p. 19/57 / 34 folpete, oxolinic acid, piperalin, proquinazide, pyroquinone, quinoxyfen, triazoxide, tricyclazole, 2-butoxy-6-iodo-3propylchromen-4-one, 5-chloro-1- (4,6-dimethoxy pyrimidin-2 -yl) -2methyl-1H-benzimidazole, 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6trifluorophenyl) - [1,2,4] triazole [1,5-a ] pyrimidine, 5-ethyl-6-octyl [1,2,4] triazole [1,5-a] pyrimidin-7-ylamine;

E) carbamates and dithiocarbamates

- thio- and dithiocarbamates: ferbam, mancozeb, maneb, metam, metasulfocarb, methram, propineb, thiram, zineb, zirame;

- carbamates: dietofencarb, bentiavalicarb, iprovalicarb, propamocarb, propamocarb hydrochloride, valifenal, (4fluorophenyl) -N- (1- (1- (4-cyanophenyl) ethanesulfonyl) but-2yl) carbamate;

F) other fungicides

- guanidines: dodine, dodine free base, guazatin, guazatin acetate, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesylate);

- antibiotics: casugamycin, hydrated casugamycin hydrochloride, polyoxins, streptomycin, validamycin A;

- nitrophenyl derivatives: binapacryl, dichloran, dinobuton, dinocape, nitrotal-isopropyl, tecnazene;

- organometallic compounds: phentin salts, such as, for example, fentin acetate, fentin chloride, fentin hydroxide;

- sulfurous heterocyclic compounds: dithianone, isoprothiolane;

- organophosphate compounds: edifenfos, fosetil, fosetil-aluminum, iprobenfos, phosphorous acid and its salts, pyrazophos, tolclofosmethyl;

- organochlorine compounds: chlortalonil, diclofluanide, diclorfen,

Petition 870160017377, of 05/03/2016, p. 20/57 / 34 flusulfamide, hexachlorobenzene, pencicuron, pentachlorophenol and its salts, phthalide, quintozene, thiophanate-methyl, tolylfluanide, N- (4-chloro-

2-nitrophenyl) -Netyl-4-methylbenzenesulfonamide;

inorganic active substances: phosphorous acid and its salts, Bordeaux mixture, copper salts, such as, for example, copper acetate, copper hydroxide, copper oxychloride, basic copper sulphate, sulfur;

biological products for fungi control, products strengthening vegetables: strain of Bacillus subtilis NRRL No. B-21661 (for example, the products Rhapsody®, Serenade® MAX and Serenade® ASO from AgraQuest, Inc., USA), strain of Bacillus pumilus NRRL No. B-30087 (for example, SONATA® and BALLAD® Plus from AgraQuest, Inc., USA), Ulocladium oudemansii (for example BOTRY-ZEN from BotriZen Ltd., New Zealand), chitosan (for example, ARMOUR- BotriZen Ltd., New Zealand).

others: biphenyl, bronopol, cyflufenamide, cymoxanil, diphenylamine, metrafenon, mildiomycin, copper oxin, calcium prohexadione, spiroxamine, tolylfluanide, N- (cyclopropylmethoxyimino- (6difluoromethoxy-2,3-difluorophenyl) methyl) -phenylacetamide, N '- (4- (4chloro-3-trifluoromethylphenoxy) -2,5-dimethylphenyl) -N-ethyl-Nmethylformamidine, N' - (4- (4-fluoro-3-trifluoromethylphenoxy) -2,5dimethylphenyl) -N-ethyl-N-methylformamidine, N '- (2-methyl-5trifluoromethyl-4- (3-trimethylsilanyl-propoxy) phenyl) -N-ethyl-Nmethylformamidine, N' - (5-difluoromethyl-2-methyl-4 - (3-trimethylsilailpropoxy) phenyl) -N-ethyl-N-methylformamidine, N-methyl (1,2,3,4-tetrahydronaphthalen-1-yl) -2- {1- [2- (5-methyl -3trifluoromethylpyrazol-1-yl) acetyl] piperidin-4-yl} thiazol-4-carboxylate, N-methyl- (R) -1,2,3,4-tetrahydronaphthalen-1-yl 2- {1- [ 2- (5-methyl-3trifluoromethylpyrazol-1-yl) acetyl] piperidin-4-yl} -thiazole -4-carboxylate,

Petition 870160017377, of 05/03/2016, p. 21/57 / 34 6-tert-butyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate, 6-tert-butyl-8-fluoro-2,3-di-methylquinolin-4-yl methoxyacetate , Nmethyl-2- {1- [2- (5-methyl-3-trifluoromethyl-1 H-pyrazol-1 yl) acetyl] piperidin-4-yl} -N - [(1R) -1,2,3, 4-tetrahydronaphthalen-1-yl] -4thiazolecarboxamide;

G) growth regulators

- abscisic acid, amidochlor, ancimidol, 6-benzylaminopurine, brassinolide, butralin, clormequate (chlormequate chloride), choline chloride, cyclanilide, daminozide, diquegulac, dimethypine, 2,6-dimethylpuridine, etefon, flumetridine, flumetralin, flumetralin, flumetralin, flumetralin, flumetralin, flumetralin, flumetralin, flumetridine, flumetralin, flumetralin, flumethyl, flumethyl, flumetrine. , gibberellic acid, inabenfid, indole-3-acetic acid, maleic hydrazide, mefluidid, mepiquat (mepiquat chloride), metconazole, naphthalenoacetic acid, N-6-benzyladenine, paclobutrazol, pro-hexadione (calcium pro-hexadione), proh , tidiazuron, triapentenol, tributylphosphorotrithioate, acid

2,3,5-triiodo-benzoic, trinexapac-ethyl and uniconazole;

H) herbicides

- acetamide: acetochlor, alachlor, butachlor, dimetachlor, dimethenamide, flufenacet, mefenacet, metolachlor, metazachlor, napropamide, naproanilide, petoxamide, pretylachlor, propachlor, tenilchlor;

- amino acid analogues: bilanafos, glyphosate, glufosinate, sulfosate;

- aryloxyphenoxypropionates: clodinafop, Cialofop-butyl, fenoxaprop, fluazifop, haloxifop, metamifop, propaquizafop, quizalofop, quizalofop-P-tefuril;

- bipyridyls: diquat, paraquat;

- carbamates and thiocarbamates: asulam, butylate, carbetamide, desmedipham, dimepiperat, eptam (EPTC), sprocarb, molinate,

Petition 870160017377, of 05/03/2016, p. 22/57 / 34 orbencarb, fenemedifame, prosulfocarb, pyributicarb, thiobencarb, trialate;

cyclohexanediones: butroxidim, cletodim, cicloxidim, profoxidim, setoxidim, tepraloxidim, tralcoxidima;

dinitroanilines: benfluralin, etalfluralin, oryzaline, pendimethalin, prodiamine, trifluralin;

diphenyl ethers: acifluorfen, aclonifen, bifenox, diclofop, ethoxyfen, lactophen, fomesafen, lactofen, oxyfluorfen;

hydroxybenzonitriles: bromoxynil, diclobenyl, ioxynil; imidazolinones: imazametabenze, imazamox, imazapic, imazapyr, imazaquin, imazetapyr;

phenoxyacetic acids: clomeprop, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, dichlorprop, MCPA, MCPA-thioethyl, MCPB, mecoprope;

pyrazines: chloridazon, flufenpirethyl, fluthiacet, norflurazone, pyridate;

pyridines: aminopyralide, clopyralide, diflufenican, dithiopir, fluridone, fluroxypyr, picloram, picolinafen, thiazopyr;

sulfonylureas: amidosulfuron, azimsulfurono, bensulfuron, chlorimuron-ethyl, chlorsulfuron, cinossulfuron, ciclossulfamuron, etoxissulfuron, flazassulfuron, flucetossulfuron, flupirsulfuron, foramsulfuron, halossulfuron, imazossulfuron, iodossulfuron, mesossulfuron, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulforon, prosulfuron, pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron, tifensulfuron, triasulfuron, tribenuron, trifloxysulfuron, triflusulfuron, tritosulfuron, 1 - ((2-chloro-6-propylimidazo [1,2-b] pyridazin-3-yl) sulfonyl) -3- (4 6-dimethoxypyrimidin-2yl) urea;

triazines: amethrine, atrazine, cyanazine, dimetamethrin, ethiozine,

Petition 870160017377, of 05/03/2016, p. 23/57 / 34 hexazinone, metamitron, metribuzin, promethrin, simazine, terbuthylazine, terbutrin, triaziflam;

urea: chlortoluron, daimuron, diuron, fluometuron, isoproturon, linuron, metabenztiazuron, tebutiuron;

other acetolactate synthase inhibitors: bispyribac-sodium, chloransulam-methyl, diclosulam, florassulam, flucarbazone, flumetsulam, metosulam, orthosulfamuron, penoxsulam, propoxycarbazone, pyribambenz-propyl, pyribenzoxin, pyracyrimide, pyriftalide, pyrachalamide, pyracyrimide, pyracidimide, pyracidimide, pyracidimide, pyrimidine, pyrimidine, pyrimidine, pyrimidine, pyrimide

others: amicarbazone, aminotriazole, anilofos, beflubutamide, benazoline, bencarbazone, benfluresate, benzofenap, bentazone, benzobicyclon, bromacil, bromobutide, butafenacil, butamiphos, cafenstrole, carfentrazone, cinidonyl, clonidone, cinidonamyl, clonidone difenzoquat, diflufenzopyr, Drechslera monoceras, endothal, etofumesate, etobenzanid, fentrazamide, flumiclorac-pentyl, flumioxazin, flupoxam, fluorochloridon, flurtamon, indanofan, isoxaben, isoxaflutol, methacryl, quenacil, propanyl, propanyl, quincyl, propanyl oxadiargyl, oxadiazone, oxaziclomefon, pentoxazone, pinoxadena, piraclonil, piraflufenaethyl, pirasulfotol, pyrazoxifene, pyrazolinate, quinoclamin, saflufenacil, sulcotrione, sulfentrazone, terbacil, tefuriltron-2-hydroxy, tetrazonone, 4-axonazone -6-trifluoromethylpyridin-3carbonyl] bicyclo [3.2.1] oct-3-en-2-one, (3- [2-chloro-4fluoro-5- (3-methyl) acetate -2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2Hpirimidin-1-yl) phenoxy] pyridin-2-yloxy) ethyl, 6-amino-5-chloro-2-cyclopropylpyrimidine-4-carboxylate methyl, 6-chloro-3- (2-cyclopropylPetition 870160017377, 05/05/2016, p. 24/57 / 34

6-methylphenoxy) -pyridazin-4-ol, 4-amino-3-chloro-6- (4chlorophenyl) -5-fluoropyridin-2-carboxylic acid, 4-amino-3-chloro-6- (4chloro-2-fluoro Methyl methoxyphenyl) pyridin-2-carboxylate and methyl 4 amino-3- chloro-6- (4-chloro-3-dimethylamino-2-fluorophenyl) pyridin-2-carboxylate;

I) insecticides

- organo (thio) phosphates: asphate, azametiphos, azymphos-methyl, chlorpyrifos, chlorpyrifos-methyl, chlorfenvinfos, diazinon, dichlorvos, dicrotofos, dimetoate, disulfoton, etion, fenitrotion, fention, isoxation, malation, metamidation, metamidation, metamidation , mevinfos, monocrotofos, oxidemeton-methyl, paraoxon, paration, fentoate, fosalone, fosmete, fosfamidon, forato, foxima, pirimifos-methyl, profenofos, protiofos, sulprofos, tetrachlorvinfos, terbufos, triazofos, triclorfon;

- carbamates: alanicarb, aldicarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, phenoxycarb, furatiocarb, metiocarb, metomyl, oxamil, pyrimicarb, propoxur, tiodicarb, triazamate;

- pyrethroids: alethrin, bifentrine, cyflothrin, cyhalothrin, cyphenothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zetacipermethrin, deltamethrin, etofenproxe, fenpropatrine, fenpropetrine, permethrin, pretrine, pyrethetrine, pretrine, pyrethetrine, pretrine, pyrethetrine, pretrine, pyrethetrine, pretrine, pyrethetrine, pretrine, pyrethetrine, pretrine, pyrethetrine, pyrethetrine, pyrethetrine, pretrine, pyrethetrine. II, resmetrina, silafluofeno, taufluvalinato, teflutrina, tetrametrina, tralometrina, transflutrina, proflutrina, dimeflutrina,

- insect growth inhibitors: a) chitin synthesis inhibitors: benzoylureas: clorfluazuron, ciramazin, diflubenzuron, flucicloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflumuron; buprofezin, diofenolan, hexitiazox,

Petition 870160017377, of 05/03/2016, p. 25/57 / 34 ethoxazole, clofentazin; b) ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide, azadiractin; c) juvenoids: pyriproxyphene, methoprene, phenoxycarb; d) inhibitors of lipid biosynthesis: spirodiclofen, spiromesifen, spirotetramate;

- Nicotine receptor agonists / antagonists: clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpiram, acetamipride, thiaclopride, 1 - (2-chlorothiazol-5-ylmethyl) -2-nitrimino-

3,5-dimethyl- [1,3,5] triazinane;

- GABA antagonists: endosulfan, etiprole, fipronil, vaniliprole, pirafluprole, pyriprol, N-5-amino-1- (2,6-dichloro-4-methylphenyl) -4sulfinamoyl-1H-pyrazol-3-thiocarboxamide;

- macrocyclic lactones: abamectin, emamectin, milbemectin, lepimectin, spinosad, spinetoram;

- mitochondrial electron transport chain inhibitor (METI) I acaricides: phenazaquin, pyridabem, tebufenepirade, tolfenpirad, flufenerim;

- METI II and III substances: acequinocil, fluaciprim, hydramethylnone;

- uncouplers: chlorfenapyr;

- oxidative phosphorylation inhibitors: cyhexatin, diafentiuron, fenbutatin oxide, propargite;

- insect inhibitors ecdysis: cryomazine;

- 'mixed oxidase function' inhibitors: piperonyl butoxide;

- sodium channel blockers: indoxacarb, metaflumizone;

- others: benclothiaz, biphenazate, cartap, flonicamide, pyridalil, pimetrozina, sulfur, thiocyclam, flubendiamid, clorantraniliprol, ciazipir (HGW86); cienopirafen, flupirazofos, ciflumetofeno, amidoflumet, imiciafos, bistrifluron and pyrifluquinazone.

[0019] In a preferred embodiment, the composition comprises a carboxylic acid amide as defined above and a

Petition 870160017377, of 05/03/2016, p. 26/57

16/34 pesticide selected from the group consisting of anilide, nitrophenyl ether, pyridine, triazole, methoxycarbamate, strobilurin, pyrazole. In another preferred embodiment, the composition comprises a carboxylic acid amide as defined above and a pesticide selected from the group consisting of tebuconazole, pyraclostrobin and fluxpyroxade.

[0020] In another preferred embodiment, the present invention relates to an aqueous composition comprising a pesticide and a carboxylic acid amide according to formula (A)

I

R2 where R2 and R3 are straight chain C4 alkyl and RI is straight chain C7 alkyl and where the pesticide is selected from fungicides, herbicides and insecticides, preferably from the group consisting of anilide, nitrophenylether , pyridine, triazole, methoxycarbamate, strobilurin and pyrazole, even more preferably from the group consisting of tebuconazole, pyraclostrobin and fluxpyroxade.

[0021] The compositions according to the invention may, furthermore, also comprise adjuvants conventionally used for agrochemical formulations, the choice of adjuvants depending on the specific form of use, the type of formulation or the active substance. Examples of suitable adjuvants are solvents, solid vehicles, surfactants (such as surfactants, solubilizers, protective colloids, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze agents, antifoaming agents, dyes, and optionally adhesives (eg for example, for seed treatment) or conventional adjuvants for bait formulations (for example, attractants, feeds, substances with bitterness).

Petition 870160017377, of 05/03/2016, p. 27/57 / 34 [0022] The compositions according to the present invention can also comprise other oil components and / or others than the carboxylic acid amides as defined above. Suitable cosolvents and oily components are water or organic solvents, such as fractions of high or medium boiling mineral oil such as kerosene and diesel oil, in addition, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols, such as methanol, ethanol, propanol, butanol and cyclohexanol, glycols, ketones, such as cyclohexanone, gamma-butyrolactone, fatty acids and fatty acid esters, and strongly polar solvents, for example amines such as Nmethylpyrrolidone. In principle, it is also possible to use mixtures of solvents and mixtures of the aforementioned solvents and water.

[0023] The compositions of the present invention can also comprise solid vehicles. Solid vehicles are mineral lands such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, shaft, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, synthetic materials of soil, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as cereal flour, tree bark, wood flour and nutshell flour, cellulose powders or other solid vehicles .

[0024] The compositions of the present invention may additionally comprise surfactants. Surfactant substances (adjuvants, wetting agents, adhesives, dispersants or emulsifiers) which are suitable for use in combination with the compositions of the present invention are the alkali metal, alkaline earth metal, ammonium salts of aromatic sulfonic acids, for example, lignosulfonic acid (types Borresperse®, Borregaard, Norway), phenolsulfonic acid, acid

Petition 870160017377, of 05/03/2016, p. 28/57 / 34 naphthalenesulfonic (types Morwet®, Akzo Nobel, USA) and dibutylnaphthalenesulfonic acid (types Nekal®, BASF, Germany), and fatty acids, alkyl- and alkylarylsulfonates, alkyl ether, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanois and fatty alcohol glycol ethers, sulphonated naphthalene condensates and their derivatives with formaldehyde, naphthalene condensates or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene-octylphenol ether, isooctyl- octyl- or nonylphenol ethoxylated, alkylphenol-polyglycolic ethers, tributylphenyl-polyglycolic ethers, polyether alkylaryl alcohols, isotridecyl alcohol, fatty alcohol / ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene ethyl ether alkyl, polypropylene ethyl ether, polypropylene ethyl lauryl, sorbitol esters, lignin sulphite liquors and proteins, denatured proteins, polysaccharides (eg methyl cellulose), modified with hydrophobes, polyvinyl alcohol (types MOWIOL®, Clariant, Switzerland), polycarboxylates (types Sokalan®, BASF, Germany), polyalkoxylates, polyvinylamine (types Lupamin®, BASF, Germany), polyethyleneimine (types Lupasol®, BASF, Germany ), polyvinyl-pyrrolidone and their copolymers.

[0025] The composition according to the invention can comprise from 0.1 to 40% by weight, preferably from 1 to 30 and, in particular, from 2 to 20% by weight of surfactants (as described above), the amount of carboxylic acid amide not being taken into account.

[0026] Suitable thickeners that can be used in a composition of the present invention are compounds that give the formulation a modified flow behavior, that is, high viscosity at rest and low viscosity in the agitated state. Examples are polysaccharides, proteins (such as casein or gelatins), synthetic polymers or layered inorganic minerals. Such thickeners are commercially available, for example, xanthan gum (Kelzan®, CP Kelco, USA), Rhodopol® 23 (Rhodia, France) or Veegum® (R.T.

Petition 870160017377, of 05/03/2016, p. 29/57 / 34

Vanderbilt, USA) or Attaclay® (Engelhard Corp., New Jersey, USA). The thickener content in the formulation depends on the effectiveness of the thickener. The person skilled in the art will choose an appropriate value to obtain the desired viscosity of the formulation. The content will be between 0.01 and 10% by weight in most cases. [0027] Bactericides can be added in order to stabilize the composition of the present invention. Examples of bactericides are those based on dichlorophene and hemiformal benzyl alcohol and also isothiazolinone derivatives, such as alkylisothiazolinones and benzoisothiazolinones (Thor Chemie's Acticide® MBS). Examples of suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerol. Examples of antifoam agents are silicone emulsions (such as, for example, Silikon® SRE, Wacker, Germany or Rhodorsil®, Rhodia, France), long-chain alcohols, fatty acids, fatty acid salts, organofluorinated compounds and mixtures thereof.

[0028] The composition according to the invention can preferably be present in the form of an agrochemical formulation. Examples of such formulations and their preparation are:

i) Water-soluble concentrates (SL, LS): 10 parts by weight of the active substances are dissolved in 90 parts by weight of water or a water-soluble solvent. Alternatively, humidifiers or other adjuvants are added. After dilution with water, the active substance is dissolved. This gives a composition with an active substance content of 10% by weight.

ii) Dispersible concentrates (DC): 20 parts by weight of the active substances are dissolved in 70 parts by weight of NMP with the addition of 10 parts by weight of a dispersant, for example, polyvinylpyrrolidone. After dilution with water, a dispersion is obtained. The active substance content amounts to 20% by weight.

Petition 870160017377, of 05/03/2016, p. 30/57 / 34 iii) Emulsifiable concentrates (EC): 15 parts by weight of the active substances are dissolved in 75 parts by weight of solvent naphtha, with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). After dilution with water, an emulsion is obtained. The composition has an active substance content of 15% by weight.

iv) Emulsions (EW, EO, ES): 25 parts by weight of the active substances are dissolved in 35 parts by weight of xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). The use of an emulsifier (for example, Ultra-Turrax), this mixture is placed in 30 parts by weight of water and transformed into a homogeneous emulsion. After dilution with water, an emulsion is obtained. The composition has an active substance content of 25% by weight.

v) The suspensions (SC, OD, FS): 20 parts by weight of the active substances are crushed with the addition of 10 parts by weight of dispersants and humidifiers and 70 parts by weight of water or an organic solvent in an agitated ball mill. give a finely divided active substance suspension. After dilution with water, a stable suspension of the active substance is obtained. The content of active substance in the composition does not exceed 20% by weight.

vi) Water-dispersible and water-soluble granules (WG, SG): 50 parts by weight of the active substances are finely ground, with the addition of 50 parts by weight of dispersants and humidifiers and formulated as water-dispersible or water-soluble granules water by means of technical devices (eg extrusion, spray tower, fluidized bed). After dilution with water, a stable dispersion or solution of the

Petition 870160017377, of 05/03/2016, p. 31/57 / 34 active substance. The composition has an active substance content of 50% by weight.

vii) Water-dispersible and water-soluble powders (WP, SP, SS, WS):

parts by weight of the active substances are ground in a rotor-stator mill with the addition of 25 parts by weight of dispersants and humidifiers and also silica gel. After dilution with water, a stable dispersion or solution of the active substance is obtained. The active substance content of the composition amounts to 75% by weight.

viii) Gels (GF): in a ball mill, 20 parts by weight of the active substances, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or an organic solvent are ground to give a thin suspension. After dilution with water, a stable suspension with an active substance content of 20% by weight is obtained.

ix) Dusts (DP, DS) 5 parts by weight of the active substances are finely ground and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dust with an active substance content of 5% by weight.

x) Granules (GR, FG, GG, MG): 0.5 parts by weight of the active substances is finely ground and associated with 99.5 parts by weight of vehicles. Conventional methods for this purpose are by extrusion, spray drying or the fluidized bed. This gives granules for direct application with an active substance content of 0.5% by weight.

xi) ULV solutions (UL): 10 parts by weight of the active substances are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a composition to be applied directly with an active substance content of 10% by weight.

Petition 870160017377, of 05/03/2016, p. 32/57 / 34 [0029] In a preferred embodiment, the compositions of the present invention are emulsifiable concentrates (EC).

[0030] In general, the compositions of the present invention comprise 0.01 to 95% by weight, preferably 0.1 to 90% by weight, of the pesticides. [0031] In most cases, the composition according to the invention comprises from 0.1 to 90% by weight, of the carboxylic acid amide, as defined above, preferably from 10 to 80% by weight and in 20 to 70% by weight.

[0032] In a preferred embodiment, the composition according to the invention comprises 60% by weight of the pesticide, as defined above, 30% by weight of surfactants as defined above, 50% by weight of the pesticides components of oil and / or cosolvents, and

0.1 to 90% by weight of carboxylic acid amide, as defined above, with the proviso that the amounts add with water to 100% by weight.

[0033] The user will generally use the composition according to the invention in a premixture device, in a backpack sprayer, in a spray tank or in an aircraft spray. Here, said composition is brought to the desired concentration with water and / or buffer, optionally with the addition of additional auxiliaries, whereby the ready-to-use spray mixture is obtained (known as a tank mixture). Typically, 50 to 500 liters of ready-to-use spray mixture are applied per hectare of agricultural area, preferably 100 to 400 liters. In specific segments the quantities can also be higher (for example, fruit growing) or lower (for example, application of

Petition 870160017377, of 05/03/2016, p. 33/57 / 34 aircraft) to these quantities. The concentrations of active substance in ready-to-use preparations can be varied within substantial ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%. [0034] Oils of various types, humidifiers, wind-reducing agents, adhesives, spreaders, adjuvants, fertilizers, plant strengthening products, trace elements, herbicides, bactericides, fungicides and / or pesticides can be added to the active substances or preparations containing them, optionally also for the mixing tank, immediately before use. These products can be mixed with the compositions according to the invention in a weight ratio of 1: 100 to 100: 1, preferably 1:10 to 10: 1. Adjuvants which are suitable in this context are, in particular: modified organic polysiloxanes, for example Break Thru S 240®; alcohol alkoxylates, for example Atplus® 245, Atplus® MBA 1303, Plurafac® LF 300 and Lutensol® ON 30; EO / PO block polymers, for example Pluronic® RPE 2035, and GENAPOL® B; alcohol ethoxylates, for example Lutensol® XP 80; and sodium dioctyl sulfosuccinate, for example Leophen® RA.

[0035] Depending on the nature of the desired effect, the application rates of the active substance, when used in plant protection are between 0.001 and 2.0 kg of active substance per ha, preferably between 0.005 and 2 kg per ha, especially of preferably between 0.05 and 0.9 kg per ha, in particular between 0.1 and 0.75 kg per ha.

[0036] The present invention also relates to a method for the control of phytopathogenic fungi and / or the growth of undesirable plants and / or infestation of undesirable insects or mites and / or to regulate the growth of plants, in which the composition according to the present invention, as defined above, it is permitted to act on the respective pests, their habit or the plants to be protected from the respective pest, on the soil and / or on undesirable plants and / or crop plants

Petition 870160017377, of 05/03/2016, p. 34/57 / 34 and / or their habitat.

[0037] Examples of suitable crop plants are cereals, for example wheat, rye, barley, triticale, oats or rice; beet, for example sugar or fodder; pomoideas, stone fruits and soft fruits, for example, apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, raspberries or currants; vegetables, for example, beans, lentils, peas, alfalfa or soy; oilseeds, for example rapeseed, mustard, olives, sunflowers, coconut, cocoa, castor, palm oil, peanuts or soy; cucurbits, for example, pumpkins / pulp, cucumbers or melons; fiber crops, for example cotton, linen, hemp or jute; citrus fruit, for example, oranges, lemons, grapefruits or tangerines; vegetable plants, for example spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, pumpkin / squash or capsicums; plants of the laurel family, for example, avocados, cinnamon or camphor; energy crops and crops of industrial raw materials, for example, corn, soybeans, wheat, rapeseed, sugar cane and palm oil; tobacco; nuts; coffee; tea; bananas; wine (dessert grapes and grapes for winemaking); hop; grass, for example peat; sweetleaf (Stevia rebaudania); rubber plants and forest plants, for example, flowers, shrubs, deciduous trees and coniferous trees and propagating material, for example, seeds and products harvested from these plants.

[0038] The term crop plants also includes those plants that have been modified by animal husbandry, mutagenesis or recombinant methods, including biotechnological agricultural products that are on the market or in the process of being developed. Genetically modified plants are plants whose genetic material has been modified in a way that does not occur under natural conditions by hybridization, mutations or natural recombination (that is, the recombination of genetic material). Here, one or more genes that, as a rule, will be integrated into the plant's genetic material in order to improve the plant's properties. Such modifications

Petition 870160017377, of 05/03/2016, p. Recombinant 35/57 / 34 also comprise post-translational modifications of proteins, oligo- or polypeptides, for example, through glycosylation or polymer binding, such as, for example, prenylated, acetylated or farnesylated residues or PEG residues.

[0039] Examples that can be mentioned are plants that, as a result of plant breeding and recombinant measures, have acquired a tolerance for certain classes of herbicides, such as hydroxyphenylpyruvate dioxigenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors ) such as, for example, sulfonylureas (EP-A 257 993, US 5,013,659) or imidazolinones (for example, US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526 , WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), inhibitors of enolpyruvylchiquime 3-phosphate synthase (EPSPS), such as , for example, glyphosate (see, for example, WO92 / 00377), glutamine synthetase (GS) inhibitors, such as, for example, glufosinate (see, for example, EP-A 242 236, EP-A 242 246 ) or oxynyl herbicides (see, for example, US 5,559,024). For example, breeding and mutagenesis gave rise to Clearfield® rapeseed oil (BASF SE, Germany), which is tolerant to imidazolinones, for example imazamox. With the aid of recombinant methods, crop plants such as soy, cotton, corn, beet and rapeseed oil have been generated that are resistant to glyphosate or glufosinate, and these are available under the brand names RoundupReady® (resistant glyphosate, from Monsanto, USA) and Liberty Link® (glufosinate resistant, Bayer CropScience, Germany).

[0040] Also included are plants that, with the help of recombinant measures, produce one or more toxins, for example, those of the bacterial strain Bacillus. The toxins that are produced by such genetically modified plants comprise, for example, proteins

Petition 870160017377, of 05/03/2016, p. 36/57 / 34 insecticides from Bacillus spp., In particular from B. thuringiensis, such as the endotoxins CrylAb, CrylAc, CrylF, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetable insecticide proteins (VIPs), for example VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematode colonizing bacteria, for example Photorhabdus spp. or Xenorhabdus spp .; toxins from animals' bodies, for example, wasp, spider or scorpion toxins; fungal toxins, for example from Streptomycetes; vegetable lectins, for example from peas or barley; agglutinins; proteinase inhibitors, for example, trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome inactivation proteins (RIPs), for example ricin, corn RIP, abrina, lufina, saporina or briodina; steroid metabolizing enzymes, for example 3-hydroxysteroid oxidase, ecdysteroid IDP glycosyl transferase, cholesterol oxidase, ecdysone or HMG CoA reductase inhibitors; ion channel blockers, for example, sodium or calcium channel inhibitors; juvenile hormone esterase; receptors for the diuretic hormone (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases and glucanases. These toxins can also be produced, in plants, in the form of pretoxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are distinguished by a new combination of different protein domains (see, for example, WO 2002/015701). Other examples of such toxins or genetically modified plants that produce these toxins are described in EPA 374 753, WO 93/07278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 and WO 03 / 52073. The methods for generating genetically modified plants are known to the person skilled in the art and explained, for example, in the publications mentioned above. A large number of the aforementioned toxins give plants that produce them a tolerance to pests of all taxonomic classes of arthropods, in

Petition 870160017377, of 05/03/2016, p. 37/57 / 34 particularly, beetles (Coeleropta), dipterans (Diptera) and lepidopterans (Lepidoptera) and nematodes (Nematoda). Genetically modified plants having one or more genes that code for insecticidal toxins are described for example in the aforementioned publications and, in some commercially available cases, such as, for example, YieldGard® (corn varieties that produce the Cry1Ab toxin), YieldGard ® Plus (corn varieties that produce the Cry1Ab and Cry3Bb1 toxins), Starlink® (corn varieties that produce the Cry9c toxin), Herculex RW (corn varieties that produce the Cry34Ab1, Cry35Ab1 toxins and the phosphinothricin enzyme N-acetyltransferase [PAT ]); NuCOTN® 33B (cotton varieties that produce the Cry1Ac toxin), Bollgard® I (cotton varieties that produce the Cry1Ac toxin), Bollgard® II (cotton varieties that produce the Cry1Ac and Cry2Ab2 toxins);

VIPCOT® (cotton varieties, which produce a VIP toxin);

NewLeaf® (potato varieties that produce the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (for example Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn varieties that produce the Cry1Ab toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (maize varieties that produce a modified version of the Cry3A toxin, see, in this context, WO 03/018810), MON 863 from Monsanto Europe SA, Belgium (maize varieties that produce the Cry3Bb1 toxin), IPC 531 from Monsanto Europe SA, Belgium (cotton varieties, which produce a modified version of the Cry1Ac toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn varieties which produce the Cry1F toxin and the PAT enzyme).

[0041] Also included are plants that, with the aid of recombinant measures, produce one or more proteins that cause an increase in resistance to, or the ability to resist, bacterial, viral or fungal pathogens, such as, for example proteins called

Petition 870160017377, of 05/03/2016, p. 38/57

28/34 related to pathogenesis (PR proteins, see EP A 0 392 225), resistance proteins (for example, potato varieties that produce two resistance genes against Phytophthora infestans from wild Mexican potato Solanum bulbocastanum) or lysozyme T4 (by example, potato varieties which, as a result of the production of this protein, are resistant to bacteria such as Erwinia amylvora).

[0042] Also understood are plants whose productivity has been improved with the help of recombinant methods, for example, increasing the yield potential (for example, biomass, grain production, starch content, oil content or protein content), tolerance to drought, salt or other limiting environmental factors, or resistance to pests and fungi, bacteria and viral pathogens.

[0043] Also understood are plants whose constituents, in particular to improve human or animal nutrition, have been modified with the help of recombinant methods, for example, oil-producing plants of long chain omega-3-fatty acids to promote health or monounsaturated omega-9-fatty acids (eg Nexera® rapeseed oil, Dow Agro Sciences, Canada).

[0044] The present invention also relates to the use of a carboxylic acid amide according to formula (A) o

Where

RI is C2-C8 alkyl, and

R2 and R3, independently of each other, are C1 -C6 alkyl, with the proviso that R2 is not C1 alkyl when R3 is C1 alkyl, as a solvent for pesticides with low or no phytotoxicity.

Petition 870160017377, of 05/03/2016, p. 39/57 / 34 [0045] In a preferred embodiment, a carboxylic acid amide, where R2 and R3 are C2-C4 alkyl and R1 is C2-C7 alkyl is used as a solvent, with little or no pesticide phytotoxicity. Most preferably, a carboxylic acid amide is used, where R2 and R3 are C2-C4 alkyl and R1 is C2-C7 alkyl as a solvent, with little or no phytotoxicity to pesticides. In an even more preferred embodiment, a carboxylic acid amide, where R2 and R3 are C2-C4 alkyl and R1 is C2 alkyl, in particular, R2 and R3 are C4 alkyl and R1 is C2 alkyl is used as a solvent with little or no low phytotoxicity to pesticides. In another preferred embodiment, a carboxylic acid amide, where R2 and R3 are C4 alkyl and R1 is C7 alkyl is used as a solvent with little or no phytotoxicity for pesticides. In a more preferred embodiment, a carboxylic acid amide, where R2 and R3 are straight chain C4 alkyl and R1 is straight chain C7 alkyl is used as a solvent with little or no phytotoxicity for pesticides.

[0046] In a preferred embodiment, no phytotoxicity means 0% of the treated plants have damage to the plant, compared to untreated plants, when determined with the phytotoxicity method, as described in the description below.

[0047] In a preferred embodiment, low phytotoxicity means 1 to 10% of treated plants have damage to the plant, compared to untreated plants, when determined with the phytotoxicity method, as described in the description below.

[0048] The phytotoxicity according to the present invention is determined by an assay in which a spray comprising water (distilled water) and carboxylic acid amide (200 l / ha comprising 1500 ml of carboxylic acid amide / ha) is prepared and applied on barley plants (cultivar Lawina) being in the phase of 3-4 leaves with a water application rate of 1.5 l / ha. The trial period lasts for 10

Petition 870160017377, of 05/03/2016, p. 40/57 / 34 days. During this time, the experimental plants receive excellent watering, with nutrients being supplied via the water used for irrigation.

[0049] Phytotoxicity is assessed by scoring treated plants compared to untreated plants, that is, treated with water only. The rating scale ranges from 0% to 100% phytotoxicity. The evaluation is performed by visual examination. 0% phytotoxicity means that there are no differences between treated and untreated plants. Thus, no phytotoxicity in accordance with the present invention means that the treated plants have no damage to the plant and there is no difference between the treated and untreated plants.

[0050] Low phytotoxicity in accordance with the present invention means that only 1 to 10% of the treated plants have damage to the plant, compared to untreated plants.

[0051] The present invention also relates to a method for the treatment of plants, thus maintaining the health of the plant comprising the step of mixing a carboxylic acid amide, as defined above, with one or more pesticides described in the present disclosure .

[0052] In a preferred embodiment, the method comprises mixing a carboxylic acid amide, where R2 and R3 are C2-C4 alkyl and R1 is C2-C8 alkyl with one or more pesticides. More preferably, the method comprises mixing a carboxylic acid amide, where R2 and R3 are C2-C4 alkyl and R1 is C2-C7 alkyl with one or more pesticides. In an even more preferred embodiment, the method comprises mixing a carboxylic acid amide, where R2 and R3 are C2-C4 alkyl and R1 is C2 alkyl, in particular, R2 and R3 are C4 alkyl and R1 is C2 alkyl with one or more pesticides. In another preferred embodiment, the method comprises mixing a carboxylic acid amide, where R2 and R3 are C4 alkyl and R1 is C7 alkyl with one or more pesticides. In another way

Petition 870160017377, of 05/03/2016, p. 41/57 / 34 of preferred embodiment, the method comprises mixing a carboxylic acid amide, where R2 and R3 are straight chain C4 alkyl and R1 is straight chain C7 alkyl with one or more pesticides.

[0053] Preferably, the carboxylic acid amide, as defined above in an amount of from 10% by weight to 90% by weight, preferably from 30% by weight to 80% by weight, is mixed with one or more pesticides .

[0054] Finally, the present invention also relates to a method for producing the composition of the present invention comprising the step of mixing a carboxylic acid amide, as defined above, with one or more pesticides.

[0055] More preferably, the method comprises mixing a carboxylic acid amide, where R2 and R3 are C2-C4 alkyl and R1 is C2C7 alkyl with one or more pesticides. In an even more preferred embodiment, the method comprises mixing a carboxylic acid amide, where R2 and R3 are C2-C4 alkyl and R1 is C2 alkyl, in particular, R2 and R3 are C4 alkyl and R1 is C2 alkyl with one or more pesticides. In another preferred embodiment, the method comprises mixing a carboxylic acid amide, where R2 and R3 are C4 alkyl and R1 is C7 alkyl with one or more pesticides. In another preferred embodiment, the method comprises mixing a carboxylic acid amide, where R2 and R3 are straight chain C4 alkyl and R1 is straight chain C7 alkyl with one or more pesticides.

[0056] Preferably, the carboxylic acid amide, as defined above in an amount of from 10% by weight to 90% by weight, preferably from 30% by weight to 80% by weight, is mixed with one or more pesticides .

[0057] The preparation of carboxylic acid amides as defined above is generally known in the art, for example, by reaction

Petition 870160017377, of 05/03/2016, p. 42/57 / 34 of an amine with a carboxylic acid, an ester or an acid chloride as described, for example, in Mitchell, JA; Reid, EE, J. Am. Chem. Soe. 1931, 1879; US 2472900; DE19650107; King, JF .; Rathore, R., J. Am. Chem. Soe. 1992, 3028.

[0058] The following examples illustrate the invention without imposing any limitation.

Examples

Example 1 - Synthesis of carboxylic acid amides [0059] N, N-dibutyl-propionamide (hereinafter dibutylpropionamide) was synthesized in a two-phase system consisting of 25% by weight of aqueous NaOH solution (625 g), toluene ( 160 ml) and dibutylamine (342 g). For the ice-cooled mixture, propionic acid chloride (189 g) was added dropwise. After the addition, the reaction mixture was stirred for 30 minutes at room temperature. The two phases were separated. The organic phase was fractionated by vacuum distillation to obtain the purified product (335 g, 90% yield).

[0060] N, N-dibutyl-octanamide (hereinafter C8 dibutylamide) was synthesized in a Dean-Stark apparatus using dibutylamine (194 g) and octanoic acid (147 g). The reaction mixture is heated to 160 ° C for 65 h. A vacuum distillation sequence provided the desired product (212 g, 83% yield).

[0061] N, N-dimethyl-propionamide (hereinafter dimethylpropionamide) was purchased from Sigma Aldrich and N, N-diethyl-propionamide (hereinafter diethylpropionamide) was purchased from TCI Europe.

Example 2 - Phytotoxicity [0062] For the greenhouse tests, barley (cultivar Lawina) was sown and grown in standard soil (type P, well) for 3 weeks. The spray mixtures were applied with a mini-compressor (4 times) in a laboratory extractor in plants being in the phase of 3-4 leaves.

Petition 870160017377, of 05/03/2016, p. 43/57 / 34 [0063] A spray comprising water (distilled water) and dibutylpropionamide from Example 1 (200 l / ha comprising 1500 ml of dibutylpropionamide / ha) was prepared and applied at a water application rate of 1.5 l /there is. The experimental period was 10 days. During this time, the experimental plants received excellent watering, with nutrients to be supplied through the water used for irrigation.

[0064] Phytotoxicity was assessed by assessing the score for treated plants compared to untreated plants, that is, treated with water only (see Table 1). The rating scale ranges from 0% to 100% phytotoxicity. The evaluation was made by visual examination. Thus, 0% phytotoxicity means that there were no differences between treated and untreated plants. The results in Table 1 demonstrate the phytotoxicity of the solvent, i.e., carboxylic acid amide, as a result of the addition of the solvent. A 0% phytotoxicity rating means no damage to the crop. A classification of 1 to 10% of phytotoxicity, indicating that the plants were not significantly negatively affected and quickly and completely recovered, is the injury limit considered acceptable by farmers. A 100% rating means complete destruction of all plants. The carboxylic acid amides of the invention, in terms of the present invention, have a phytotoxicity below 10% which means that less than 10% of the plants showed necrotic damage. Thus, less than 10% of the plants were affected when the aforementioned carboxylic acid amides were applied on the plants, at a dose of 1500 ml / ha. However, through the application of dimethylpropionamide, a non-inventive carboxylic acid amide, on plants, up to 43% of plants showed necrotic damage. Thus, carboxylic acid amides in which the N, N-alkyl groups are having more than two carbon atoms appear to have no or almost no phytotoxic effects on plants and can therefore be used in agricultural compositions to reduce phytotoxicity

Petition 870160017377, of 05/03/2016, p. 44/57 / 34 in such compositions.

Table 1: Phytotoxicity [%] 10 days after treatment

Carboxylic acid amide Phytotoxicity [%] _ a) 0 Dimethylpropionamide ^b) 43 Diethylpropionamide 6 Dibutylpropionamide 0 Dibutylamide Cs 5

a) Control experiment, non-inventive, without carboxylic acid amide.

b) Comparative experiment, not inventive.

Example 3 - Determination of maximum solubility [0065] The respective fungicide was dissolved in the solvent of interest, so that a supersaturated solution was obtained. The deposit was filtered. The concentration of the fungicide in the supernatant was determined using quantitative 1H-NMR spectroscopy.

Table 2: Solubility [%] of different fungicides in carboxylic acid amides

Carboxylic acid amide Solubility [%] Tebuconazole Solubility [%] Pyraclostrobin Solubility [%] Fluxapyroxade Dimethylpropionamide 54 70 53 Diethylpropionamide 49 62 13 Dibutylpropionamide 38 42 28 Dibutylamide Cs 27 24 13

Petition 870160017377, of 05/03/2016, p. 45/57

Claims (8)

1. Aqueous composition, characterized by the fact that it comprises a pesticide and a carboxylic acid amide according to formula (A)

(Where RI is C2 alkyl and R2 and R3, independently of each other, are C4 alkyl, with the proviso that R2 is not C1-6 alkyl when R3 is C1-6 alkyl, under the condition that the pesticide is not chloridazon, bromopyrazone or carbamate. 2. Composition according to claim 1, characterized by the fact that the pesticide is selected from fungicides, herbicides and insecticides. Composition according to claim 1 or 2, characterized in that the composition comprises from 0.1% by weight to 90% by weight of carboxylic acid amide. Composition according to any one of claims 1 to 3, characterized in that the composition comprises 5 to 60% by weight of the pesticide, 1 to 30% by weight of surfactants, 0 to 50% by weight of the oil and / or cosolvent components, and 0.1 to 90% by weight of carboxylic acid amide, with the proviso that the amounts add water to 100% by weight. Petition 870190102650, of 11/10/2019, p. 8/10 2/2 5. Method for controlling phytopathogenic fungi and / or growth of undesirable plants and / or infestation of undesirable insects or mites and / or for regulating plant growth, characterized by the fact that the composition, as defined in any one of claims 1 to 4, it is left to act on the respective pests, their habit or the plants to be protected from the respective pest, on the soil and / or on undesirable plants and / or the crop plants and / or their habitat. 6. Use of a carboxylic acid amide according to formula (A) o

Where RI is C2 alkyl, and R2 and R3, independently of each other, are C4 alkyl, with the proviso that R2 is not C1 alkyl when R3 is C1 alkyl, characterized by the fact that it is a solvent for pesticides with low or no phytotoxicity. 7. Method for treating plants, thus maintaining the health of the plant, characterized by the fact that it comprises the step of mixing a carboxylic acid amide, as defined in claim 1, with one or more pesticides. Method for producing a composition as defined in any of claims 1 to 4, characterized in that it comprises the step of mixing a carboxylic acid amide as defined in claim 1, with one or more pesticides.